Planning is underway for new NASA missions to the moon and to MARS. These missions carry a great deal of risk, as the Challenger and Columbia accidents demonstrate. In order to minimize the risks to the crew and the mission, risk reduction must be done at every stage, not only in quality manufacturing, but also in design. It is necessary, therefore, to be able to compare the risks posed in different launch vehicle designs. Further, these designs have not yet been implemented, so it is necessary to compare these risks without being able to test the vehicles themselves. This paper will discuss some of the issues involved in this type of comparison. It will start with a general discussion of reliability estimation. It will continue with a short look at some software designed to make this estimation easier and faster. It will conclude with a few recommendations for future tools.